On June 12, 1968, following his graduation from Harvard, he was commissioned in the Naval Reserve and rose to the rank of lieutenant on July 1, 1971.

from Harvard Law, Roosevelt spent 10 years as partner at Choate, Hall & Stewart in Boston, Massachusetts.

Roosevelt was the associate commissioner for Retirement Policy for the Social Security Administration before joining Tufts Health Plan in 1999 as senior vice president and general counsel.

[4] In 1986, he ran for Congress in Massachusetts's 8th congressional district, losing the Democratic primary to Joseph P. Kennedy II.

He was called upon in 2008 to oversee hearings on controversies related to seating delegates from Florida and Michigan to the 2008 Democratic National Convention.